Her Sisters Professor
by Swen1999
Summary: When her sister moves with her to New York City for school, Emma Swan's life dramatically changes. She finds her self in love with the new freshman English teacher, Regina Mills. What will happen after a meeting with Professor Mills commences? SwanQueen AU.
1. Getting Started

Home. What is home? Growing up in the foster system, Emma Swan had no sense of what home was. She had nowhere to call home. The only place that felt like home was her apartment in New York. It was small but it worked. However, it felt empty. She had nothing but a couch, a dresser, and a bed, but that's all she needed really. But that was about to change. Her sister Ruby was ready to join her in the big city.

When Emma arrived at the group home where her sister lived, she was ecstatic. She couldn't believe that her baby sister was coming to New York. Now that they are both finally out of the system, they can begin to live their normal lives together.

"Rubes?!" Emma screamed with joy. It had only been two weeks since she had last seen Ruby, but it felt like a lifetime. Emma wanted to take Ruby with her when she first left for New York. However, due to Emma's young age and inability to provide for both of them, the state wouldn't allow Ruby to leave with her. Every other week, Emma would drive up to Boston to visit her sister. But now Ruby was 18 and was finally out of the system.

"Emma!" Ruby belted as she ran toward her sister. Emma has always picked Ruby up when they hugged, but this time it was different. This time she knew that Ruby would be coming home with her. Home. Emma's apartment would now be both of their homes. They both were home to each other.

"So, are you excited?" Emma asked, setting Ruby down. Ruby was finally joining her sister in New York for school. Emma was in her senior year at New York University's School of Law, earning her degree in Criminal Justice. She was glad that her sister had chosen what seemed like an easier degree program. Ruby had been accepted into NYU to earn her degree in Business Management. Ever since she was a little girl, she has wanted to own her own restaurant.

"I am beyond ready to get out of this place. I honestly don't know how I've been able to survive these last 3 years without you here." Ruby said as they walked to the back of the yellow bug.

"Well, from now on you won't have to worry about that." Emma said, placing Ruby's sole suitcase in the trunk. She closed the hatch and put her arm around her sister. "Come on, let's go home."

They got in the bug and began their four hour journey to The Big Apple.

** 3 Hours Later **

"So, have you gotten your class schedule yet?" Emma asked. She was trying to make conversation because it had been quiet for a painful amount of time.

"Not yet. I should pick it up on Monday before class. How are the teachers there? I heard that in the first year of college, no matter the major, we have to take certain classes."

"The teachers I had were pretty good. But, most of them have either left the school or have moved up to teach classes focused to more specific majors. The only teacher that I had and still teaches freshies is Doctor Blanchard She teaches History, and she was one of the nicer teachers I had."

"Is the campus confusing to get around?"

"Not as confusing as the rest of the city. But you get used to it after a while." Emma could tell that Ruby was nervous. But, who could blame her? The biggest city either of them had ever lived in was Boston and it was nothing compared to what was about to come.

The next hour passes as Ruby asks a million and one questions to which Emma has a million and one answers.

"Seen any plays since living in the city? I know you said you were going to try to catch at least one before I came." Ruby asked. Both of them loved the theater, but neither of them had seen a professional play in ages.

"Not yet. Do you know how expensive those things are?" Emma said, pulling onto the curb in front of her apartment building. "Maybe, when we can get some money saved up, we can go to the theater." Emma said, stepping out of the bug.

"That would be great." Ruby said, closing the car door. "We could go see Hamilton. I heard it's doing great, and it sounds really cool."

"It would be cool, but good luck getting tickets. I checked into them not too long ago but they're sold out until next year. We'll probably have to settle for Wicked or something." Emma said, retrieving the suitcase from the back.

"Yeah, you're probably right." Ruby said.

They walked into the apartment building and Emma headed for the stairs.

"Why don't you use the elevator?" Ruby asked, pointing to an old elevator.

"The damn thing never works. It did when I first moved in, but even then, it was sketchy as hell." Emma said beginning to walk up the stairs.

When they got to the door, Emma stopped to fumble with her keys. She had been wanting to tell her sister something for awhile now and she was contemplating on telling her tonight.

"Are you okay?" Ruby asked, seeing that Emma was having some issues.

"Yeah. Just . . . excited that you finally get to see the place." Emma said, putting the key in the door. She opened the door, spreading her arms out wide. "Welcome home!"

Ruby immediately noticed the lack of furnishing. She looked around, and saw the small, tattered brown couch.

"I know it's not much, but I've been saving up so that when you got here I would have enough money until we both have jobs." Emma had been working down at the diner on 51st Street. She got paid next to nothing, and was basically living off of the tips people left. Good thing some people were generous.

"It's great." Ruby said. "So, can I just put my bag in your room?"

"Yeah, sure." Emma said. While Ruby stepped into the other room, Emma began to make some hot cocoa. She was ready to tell her sister.

Ruby changed into her pajamas while in Emma's room. When she came back, her sister had hot cocoa made. She knew something was up. "Okay, what's going on Emma? You never make cocoa unless you're anxious or on your period, and I know it's not the latter. So, what's up?" Ruby asked.

"Okay, you caught me. Sit down." Emma said, handing Ruby her cocoa. Ruby sat down and looked up at Emma with concern. *Sigh* 'Okay, Emma. You can do this' she thought. "I'm not really sure how to tell you this, so I'm just gonna say it. I like girls." Ruby just kind of looked blankly at her for a second. "I'm gay." Emma said, hoping to clarify her previous statement.

"Oh my God. Emma, I am so proud of you." Ruby said, jumping up to give her sister a hug. "I can only imagine how hard that must have been for you. I love you and I am always going to support you. Know that." Emma's eyes began filling up with tears.

The rest of the night went by really smoothly. They took time to catch up and just talk. They both decided to go to bed pretty early that night, because the next day was registration day.


	2. Registration Day

Going from teaching high school to college was going to be a big step, but Regina Mills was ready for it. She had always wanted to become a college professor, but after the loss of her father, she decided to teach high school and stay close to home in Maine. Five years have passed and Regina is now beginning to fulfill her dreams by teaching freshman English at NYU. Today was to be her first day on campus and she was anxious beyond belief.

She arrived at the campus a little early that morning, for she knew that she had to hand out registration papers. Before meeting up with other faculty members, she decided to go set her small box of things in her new office. She looked around and the small room. In it, she noticed a medium sized mahogany desk and two office chairs. She sat her things down and retreated to the registration office to grab the papers she was to hand out.

Not long after the day began, Regina was already starting to feel tired. She had been up late the previous night with her three year old son, Henry. Feeling the exhaustion hit, she decided to retreat back to her office to begin setting up for class on Monday. She asked one of the other professors to take her place, explaining how late she had been up the previous night.

While setting up her office, a girl of medium height and brunette hair walks in. Regina notices the edginess of the girls clothes and assumes that the girls must have wandered in there by accident.

"Hello. ? I'm Ruby Swan. I'll be in your class this semester." Ruby says offering out her hand.

"Nice to meet you, Ruby." Regina says shaking Ruby's hand.

"I'm sorry if I interrupted you, I'm just trying to learn the campus and find where my classes are." Ruby says, sitting down in the office chair in front of Regina's desk.

"You are perfectly fine, dear. I was just finishing up a few-" Regina was interrupted by her phone ringing. It's Henry's babysitter, Caitlin. "I'm sorry. Could you excuse me for just one moment?" She said stepping out of the room.

"Hello?"

"Hey, Regina." Caitlin said. She could hear the worry in Regina's voice, so she knew she needed to explain how he was acting in the best way possible. "Look, I know you're busy, but Henry is acting weird. He's very lethargic and moody today. I think he may be getting sick."

"Yeah, he was acting strange last night. Just hold tight. I'll be there shortly." Regina said, Hanging up the phone.

Regina walked back into her office, where she saw Ruby looking at the picture she had placed on her desk just minutes ago. It was taken the day Regina had adopted Henry. The picture was Regina holding holding Henry wrapped in a blue blanket. Regina had always cherished that picture, because that was the day that changed her life for the better. That was the day she finally felt at peace with the world.

"So, you have a son?" Ruby asked.

"Yes, I do. His name's Henry. I actually have to-"

"I don't see any pictures of his father anywhere."

"He's actually adopted. Look, I have to leave. That was his babysitter who called; he's sick. But, I'll uh see you on Monday. Okay?" She said picking up her purse.

Ruby nodded her head and stepped out side of the door. "It was really nice meeting you ." she said before walking off to find the offices of her other teachers.

Regina rushed to her car. Henry has never acted the way he has the past few days. Lately, he seems to have had no energy, and for most three year olds that's unusual. The adoption agency had warned Regina of any possible health problems that could be passed genetically. Since it was a closed adoption, there was no way of knowing if either birth parent had any type of genetic problem that could've been passed on to her son. And that's what scared Regina more than anything. She hated the idea that something could possibly be wrong with her little angel.

While in the car, Regina called the doctor and explained how Henry's been acting. He told her to bring him in and he would check him out and see if there was any cause for concern.

When she arrived at her apartment, Caitlin was already waiting on her. She explained how he's been acting since she had gotten there that morning.

"This is very unusual for him." Caitlin said. She had been watching Henry for a little over a year now and she was very concerned.

"I know. I've called Doctor Whale and he's told me to bring him to his office for a check up." Regina said, picking him up. "How are you feeling, buddy?" She asked

"Sweepy." Henry said, rubbing his eye.

"Well, mommy needs you to wake up so we can go see the doctor so you won't be sleepy anymore. Can you do that for mommy?" Regina asked. Henry nodded his head and placed it on his mother's shoulder. "That's my boy." Regina said smiling. "Caitlin, you are more than welcome to stay here or go with us if you like."

"No thank you, Regina. I really should be heading out. I need to get supplies for school on Monday, and I need to run by my mom's and grab the rest of my things." she said, gathering her purse.

"Oh, you're moving out of your mother's house?"

"Yes ma'am. I've decided, since I'm a senior in college I should probably move out and start becoming my own person. I found a nice, small apartment in East Village."

"That's nice." Regina said, walking out of the apartment. "Well, tell Katherine I said hello, and I'll be sure to tell you what the doctor says."

"I will. Love you guys." Caitlin said, heading down the stairs.

"Love you too." Regina said.

The Uber ride to the doctor's office seemed to take an eternity. From the time that Regina and Henry left the apartment to the time they arrived at the doctor's office, Henry had fallen asleep again. Regina woke him up and carried him in the building.

"Hi. My name is Regina Mills. I have an appointment for my son today." She said, approaching the receptionist.

"Alright, . What's your son's name?"

"Henry. Henry Daniel Mills." Regina said.

The receptionist typed in his name and saw Henry's appointment come up on the screen. "Okay, . Would you and Henry follow me, please?" She said, walking towards the door that lead to the examination rooms. The receptionist then showed Regina and Henry to examination room 4. " will be with you shortly." She said, closing the door behind her.

Regina and Henry were sitting in examination room alone. Regina was lost in her own subconscious thoughts while Henry was playing with her phone. Henry looked up and asked "Mommy? Am I going to be okay?"

Regina looked down at him and smiled. "Of course you are my little prince. Everything will be just fine." Right as she finished her reply, walked in.

"Hey, Henry. How are ya feelin' buddy?" He said, walking over to the toddler.

"I'm sweepy. Mommy's been keepin' up to come hewre." He said.

"Well, let's see if we can find out what's going on. Okay, buddy?" he said, picking him up and placing him on the examination table. "Hey, Regina. Come here for a second." Whale said. He noticed that Henry's neck seemed a bit swollen. Maybe it's an allergic reaction to something? "How long has his neck been swollen like this?" he said, placing his fingers on Henry's throat.

"That tickews." Henry said squirming and giggling.

"Can you be still for me buddy?" the doctor asked. "Thank you."

"It's been there since the day I adopted him. I just assumed it was his baby fat." Regina said.

"It doesn't feel like baby fat. I think his thyroid may be swollen. You said his case was a closed adoption, right?"

"Yes." Regina said glaring at him. "What does that have to do with anything?"

"Well, Hypothyroidism is another name for an underactive thyroid. It can be a genetic trait that is passed on. Some symptoms are lethargy, swollen thyroid, and mood swings, all of which you said he's been displaying. I'd like to send him for an ultrasound and a blood test. This will determine if it is indeed hypothyroidism or something else."

"Well, what if it is hypo-..."

"Hypothyroidism. If it is, then he will be placed on a low dosage of levothyroxine, a medicine that will help his thyroid start working again."

"How long would he have to be on the medicine?" Regina asked. She was beginning to become more worried. She could read the concern on the doctor's face, and honestly she thinks he's lying about the severity of the situation.

"He would be on it probably the rest of his life. As he gets older, the dosage would have to be upped but that's normal. Let's not worry about the what ifs right now," he said, lightly grabbing Regina's arms. "Okay?"

"Alright." Regina said. "When do you want to do the ultrasound and stuff?" she asked.

"We can do both the blood test and the ultrasound tomorrow, if you want."

"That would be fine." Regina said.

"Well, buddy, looks like you'll see me again tomorrow." said, turning to Henry.

"Owkay." He said. "Am I stiww goin' to be sweepy?"

"Maybe. Some days you might be sleepy and other days you might feel like you could run around the world."

Doctor Whale made the appointments for the next day. On the way home, Regina tried to explain to Henry that everything would be okay. After putting Henry to bed that night, Regina frantically stayed up researching hypothyroidism and the affects it could possibly have on the little boy that stole her heart so long ago.


	3. Late Birthday Present

After Registration was over, Ruby decided to go back to the apartment. Walking around campus wore her out more than anything she could remember. But, at this point, she was more worried about riding the subway alone. Afterall, she had only been in NYC for one day. She remembered what her sister had told her: "If anyone so much as look at you funny, just call me. It makes them less likely to mess with you."

Much to her surprise, Ruby had no problems on the subway. However, she decided to call Emma until she got to the apartment. She felt safer just hearing her sister's voice. When she walked in, she saw Emma in the kitchen making sandwiches.

"So . . . ? How was it?" Emma asked. She had been waiting all day to hear what Ruby thought about the campus and her teachers.

"Well, I met two of my teachers." she said, sitting her her papers and purse on the counter. "The other's were too busy helping out with registration."

"Really? Which teachers did you meet?"

"Well, I met Doctor Blanchard. I caught up with her after grabbing my papers. She seems really nice, although I don't know if I'll like her class though. I heard she's pretty tough." she said, grabbing a drink out of the fridge.

"Yeah, she is. But you can handle it." Emma said, heading over the the couch. "Who else did you meet?"

"I met my English professor, Professor Mills."

"Oh? I don't think I've heard of her." Emma said, taking a bite of her sandwich. "Did she seem nice?"

"Yeah. She seemed great. I went to her office when she was setting up. She seemed like a pretty open person." Ruby said. After a moment she noticed that Emma was looking at her like she wanted her to go on. "Not long after I got there, her phone rang, and while she was gone I was looking around on her desk at the pictures she had. I found out that she has a son."

"That's nice. Was her husband good looking?" Emma asked. Ruby raised an eyebrow. "What? Just because I'm gay, I can't think men look good?"

"Sorry." Ruby said laughing. "I don't think she's married. Or, even has a boyfriend for that matter."

"Oh . . . So the kid is from a past relationship then?"

"I asked that actually. She said he's adopted." Ruby said, taking a sip of her drink.

"Wait a minute. You straight up asked her if the kid was from a past relationship?" Emma asked, laughing. "Really?"

"Yeah. And anyways I had a good reason. He's a cute kid."

"I'm sure he is. Anyways, enough about school and the kid. I want to take you out tonight." Emma said, standing up to throw away her plate.

"Emma, you don't have to do that. We don't have to go out."

"I know, but I want to take you out. Trust me you'll love it. Consider it a late birthday present." Emma said, heading to her bedroom.

* * *

After several hours of research, Regina called Caitlin. With all of the events of that day, she felt like she needed to unwind.

"Regina?" Caitlin answered, "Is everything okay?"

"Not really. Doctor Whale seems to believe that Henry has Hypothyroidism." Regina informed.

"Oh my. Is he going to run any tests to make sure?"

"Yes. Doctor Whale scheduled them for tomorrow…" Regina said. She waited a few moments before following up with a favor. "What are you doing tonight?"

"I'm just staying at mom's tonight. Why?"

"I was wondering if you could come over in case if Henry wakes up. I really need to go get my mind off of things."

"Of course! I'll be there in a few."

Regina began to get ready. Earlier, she thought of going to the club that she went to a few years ago when she was visiting Katherine after her father died. She remembered how she felt that night. She also remembered the girl she hooked up with that night. But, she was determined not to go home with anyone tonight. She just wanted to let loose and have fun.

* * *

"Will you please tell me where we're going already?" Ruby begged.

Emma had decided to keep the destination a secret from her sister. So, she made Ruby wear a blindfold. She wanted to keep the surprise for as long as she could. Emma was taking her to The Smash Nightclub near Times Square.

This club was notorious for its extravagant nightlife. Every night music, dancing, and drinking would carry on well into the early hours of the morning.

Not long after moving to the city, Emma's roommate took her to The Smash. That night, she danced and drank more than she could remember. But, she does remember it being one of the best nights of her life.

"I told you, I'm keeping it a surprise for a reason. Trust me you'll love it." Emma said.

A few minutes later, they pulled into the back parking lot of the club. Emma helped Ruby get out of the bug and began to walk towards the front entrance. As they got to the door, Emma handed the security guard a note. He read it and motioned her to lead Ruby in.

When they walked in, Ruby could hear loud music booming and see lights pulsing through her blindfold. Before she knew it, Emma ripped off her blindfold. She was delighted to see that she was standing in the midst of one of the biggest clubs in the city.

"Oh my God! Emma!" she screamed, giving her sister a big hug. "How did you get us in here?"

"Let's just say I have some connections." Emma laughed. "I wanted you to have a proper Friday night in the city. How about I go grab some drinks so you can get your night started?"

"But, I can't drink yet…"

"Don't worry. I'll slip you some." Emma winked.

She headed to the bar.

"Two tequila shots please." Emma asked the bartender. She noticed a woman sitting next to her with a drink in hand. She seemed to be alone and slightly depressed. "Not having fun?"

"No, it's not that. I just seem to have a lot on my mind." the woman said.

"You wanna talk about it?" Emma asked.

"It's my son. He's really sick and I'm afraid it's much more serious than what the doctor thinks it is."

"Aw, I'm so sor-"

"Here are your shots, ma'am." the bartender said.

"Thank you. Could you give me just a second? I need to take this to my sister." Emma said.

"Sure."

Emma found her sister on the dance floor and told her she could have both drinks. She immediately headed back over to the bar. The woman was still sitting there.

"I'm back. Sorry about that."

"It's fine. You didn't have to come back. You should be enjoying your night here with your sister." the woman said.

"It's fine, really. I'm not much of a partier. I brought my sister here as a sort of late birthday present."

"Well that was incredibly nice of you." the woman said, smiling.

Emma noticed how beautiful of a smile she had. She also noticed her beautiful brown eyes to match her dark brown hair. "My name's Emma, by the way." she said, smiling back and offering a handshake.

"Regina" the woman said, shaking the blonde's hand.

"Nice to meet you, Regina."


	4. Walking and Talking

**A/N: Hey guys! Sorry, I know it's a short chapter, but I promise that the next two chapters are going to be much longer. Enjoy! :)**

* * *

"It's a pleasure to meet you, too, Emma." Regina replied. "However, I really should be going. I can't even hear myself think in here."

Emma wanted to talk to the woman because she seemed distressed. The thought of Regina leaving now made Emma worry that she had said something wrong or scared her off.

"How many drinks have you had tonight, Regina?" Emma asked.

"Excuse me? I'll have you know that I am mo-"

"How many drinks have you had tonight?" Emma repeated.

Regina looked down in dismay. "I honestly don't know. I lost count sometime ago."

"Do you need me to call a cab or an Uber for you?" Emma was genuinely concerned for Regina. Anyone that's lived in New York knows that it's not safe to walk the city streets at night, especially alone.

"No. I don't live far. I'll just walk home. I would hate to be a burden on you," the older woman replied.

"Well, in that case, let me walk you home. I insist." Emma said, stepping off of the stool she was once sitting on.

"Won't your sister notice your absence?"

"No," Emma said. She looked over to see that Ruby was being the life of the party and dancing her life away. "I don't think she'll even notice I'm gone. Besides, I want to hear about your son."

The women gathered their things and began to leave the club. As they stepped outside, Emma was finally able to see Regina clearly. She noticed that she was wearing a white blouse and a black skirt. What was a woman like that doing in a place like that? Emma shrugged it off and decided to strike up the conversation again.

"So, you were talking about your son? You said he was sick, right?" Emma asked, hoping she would want to talk about it.

"Yes," Regina said, beginning to walk. "His name is Henry, and he's three."

"That's an unusual name to hear these days." Emma said.

"It was my father's name." Regina said. She looked down at her feet as she walked then remembered she was talking about the events of the day. "Anyway, the past few days he's been very lethargic and acting weird. So, I took him to the doctor today to see if we could find out the problem. He told me that Henry might have Hypothyroidism. So, on Monday I have to take Henry to have an ultrasound and blood work done to make sure it's that and not thyroid cancer."

Emma listened to the woman with a deep interest. She had always loved when people talk about their kids with such admiration. But, this was different. Hearing Regina talk about her son made it seem like she had known her for a lifetime.

"You know, my sister has that. Hypothyroidism, I mean. She was diagnosed with it when she was fifteen. The doctor's told us that it was probably passed down from our parents, but there was no way of knowing for sure since we were put into the foster system when I was three." Emma said. Regina's head shot up and looked at her with a puzzling look. "My parents gave us up not long after she was born. We were both in the system, living in foster and group homes, until we both turned eighteen. That's why we were out celebrating. It's her first real night in the city."

"My son is adopted. I adopted him when he was just three weeks old." Regina replied. "Doctor Whale told us the same thing. He said that it was probably passed down from Henry's birth parents, but I'll never know because it was a closed adoption."

"Sounds like the kid and I have a lot in common. Of course, I wasn't lucky enough to grow up with amazing parents, such as you and your husband."

"What? No. I'm not married." Regina replied.

"Really?!" Emma questioned. "A beautiful, dignified woman such as yourself hasn't been snatched up, yet?"

Regina blushed and glanced down at her feet smiling. "Nope. I haven't really been one to put myself out there like that. What about you? I'm sure that someone of your charm and grace must have a guy lucky enough to call you his."

"Not exactly. Guys I know aren't really into me like that." Emma said. She could feel her face flushing because of what she was going to say next.

"Really? Why do you say that?" Regina asked.

"Because, I'm gay." Emma said. She was afraid of the judgement that would follow, because she knew that the society around her still didn't approve of gay people.

Regina stopped as soon as Emma said it. She looked at her for just a moment, then embraced her with a hug. "I am, too. And, I know how hard it is to say it especially with the way things are today."

In that moment, Emma felt relief. She returned that hug, and as she pulled back, the woman grabbed her face and said, "Never let someone's judgments stop you from being who you are."

Regina looked up, "Well, this is my place. I would offer you to come in and have a drink, but seeing as though I'm already drunk and my son is in bed asleep, I'll have postpone that offer to another time."

Emma smiled. "In that case, let me give you my number, so I can take you up on that at another time."

Regina pulled out her phone and they exchanged numbers. "Well, I guess it's goodnight, then. Thank you for listening to me tonight."

"Anytime," Emma smiled.

Emma returned to the club. Ruby, in fact, did not notice her absence, and Emma was able to dodge the never ending questions she knew her sister would ask, if she were to have found out.


	5. Aftermath

**A/N: Hey guys! Like I promised, this is a much longer chapter. I would really enjoy hearing some feedback from you :) PM me here or message me on Tumblr Swen1999. (You can follow me there too if you'd like)**

* * *

The next day, Regina woke up with a pain splitting headache. She looked over at her alarm clock to notice that it was well after noon. She closed her eyes for a moment, only to immediately register what today was. In that moment, she jumped up, grabbed her robe, and headed to the living room. When she walked in, Regina saw Caitlin and Henry sitting on the couch, watching cartoons.

"Look who finally decided to wake up!" Caitlin exclaimed. She noticed that Regina winced at the statement. With a grin, she turned to Henry and said, "Henry, why don't you tell your mommy good morning."

As Henry got off of the couch, Regina glared at Caitlin and mouthed, 'We need to talk'. Henry then proceeded to run and jump into his mother's arms. Regina embraced her son as she picked him up. "Good morning, sweetie. How's my boy feeling?"

"I'm feeling gweat mommy!" he screamed.

A loud ringing began to occur in Regina's ear. She couldn't remember how much she drank, but she knew it was too much. She put Henry down and told him to go back to watching cartoons. She then motioned for Caitlin to follow her to her bedroom. Caitlin obliged, and Regina softly closed the door behind them.

"How are you feeling?" Caitlin asked as she flopped down on Regina's bed. She could feel the glare Regina was giving her. "I mean you should feel good after talking to that girl last night," she said as she was sitting up.

Regina widened her eyes. "What are you talking about? What girl?"

"You don't remember? Oh, boy. You really were hammered." Caitlin laughed, falling back on the bed again. "You came home, obviously drunk off your ass, and you would NOT stop talking about this blonde that you met." She paused for a moment. When she sat up, she saw Regina looking through her phone. "Oh yeah, and you were texting her like crazy. Not really sure if she was able to make sense of the nonsense you were attempting to type, though. What was her name? Emma?"

Regina went to her messages. Sure enough, there were several messages between her and a girl named Emma.

R - Thank you for walking me home. Maybe we'll do it again sometime ;)

E - Maybe, but I'd rather for you to be sober.

R - PPPSSSHHHH I'm fine. Hey, how about you go to dinner with me tomorrow night. My treat.

E - I don't know. Are you sure?

R - Of course. Meet me in front of my building tomorrow night at eight.

E - If you insist. I'll see you then. :)

R - It's a date ;)

"Oh my god . . . I can't believe I did this." Regina said, giving her phone to Caitlin. She walked over and sat next to her on the bed. She watched as Caitlin read the messages and could already feel her judgment.

"Well, I guess you have a date tonight." Caitlin smiled. "Wait, didn't Henry have a doctor's appointment today?"

"Shit. You're right. He was supposed to fast, but I'm sure he's already eaten breakfast. I'll have to call to reschedule." Regina said. "As for that date, I might have to do the same."

"No! You should go! The way you were talking last night, she sounded really sweet. Besides, you need to get out more, to be honest." Caitlin said.

"Gee, thanks," Regina said. "I don't even remember meeting her. I don't even know where to take her, or what to wear, or anything. Do you know how long it's been since I've been on a date?"

Caitlin glanced over at Regina. In that moment, she could see why her mother made a friend with this woman. Regina was just like her mother; she overreacted about everything, but still is able to find a way to make everything okay. "You'll be fine, Regina. Don't worry about Henry. I'll call the doctor and reschedule it for next Saturday since this is the first week of school. You just need to find a place to take Emma to, and get ready for your date."

"But . . . I don't even know what to wear . . ."

* * *

"So . . . ?" Ruby asked. "Are you excited?" Ruby found out about the event of the previous night that morning. At first, she was a little hurt that Emma left her for some stranger, but then she realized that her sister did the right thing. She made sure that someone made it home safe.

Emma was going through everything in her closet, trying to find something to wear for her date with Regina. She didn't even know where they were going, let alone what to wear. It had been over a year since her last date; so needless to say, she was nervous. "I'm a fucking train wreck. I haven't been on a date in so long. And, who's to even say this is a date? She was super drunk, so maybe she meant it rhetorically. Like, how when you make plans with friends you say 'it's a date'. But, the winky face says otherwise." Emma sat down on her bed and put her face in her hands. "Oh my god. I'm so fucking stupid. I shouldn't have accepted."

Ruby sat down beside her sister and wrapped her arms around her. "It's okay, Emma. If it's meant to work out, it will. Just don't even think about it being a date. Like you said, it may not even be a date. Maybe she wants to pay you back for making sure she got home okay. Either way, you're going to dinner. Wear something comfortable. Not too dressy, not too casual."

Emma shook her head and hugged her sister. It felt weird having to hear it coming from her little sister, but she was still glad to have received it. She got up, found some clothes, and got ready. Now, it was time for her to head to Regina's for her 'big date'.

* * *

As Emma approached Regina's building, she began to feel calm. She had nothing to really be nervous about anyway. After all, Regina seemed to be a genuinely nice person. Emma looked down at her watch. 7:45. Okay, so maybe she was a little nervous. Then again, it had been over a year since her last date.

Emma decided to text Regina.

E - Hey, uh, I'm downstairs. I know, I'm early.

Emma patiently waited for a response. A couple of minutes had passed when she felt her phone buzz in her pocket.

R - Okay. I'm not quite ready yet. Come on up. I'll buzz you in. Number 108.

Emma stared at her phone, as a knot began to form in her stomach. She entered the building and approached the elevator. She didn't even know what floor her apartment was on. This could take a while. While she was waiting for the elevator, a young woman approached her. She seemed like she knew building pretty well.

"Excuse me, do you know which floor 108 is on?" Emma asked.

The young woman's eyes widened. "You must be Emma! Damn, Regina was right."

"Excuse me?" Emma said.

"Sorry, I'm Caitlin. I babysit her son Henry from time to time. I'm actually watching him tonight." Caitlin said as the elevator doors are opening. "Just follow me. I'll take you there."

Emma followed Caitlin into the elevator. As the doors closed, she could feel the awkwardness in the space. The elevator stopped on the tenth floor. Exiting the elevator, Emma asked, "Which way?"

"Just follow me."

Caitlin took a left. Thankfully, Regina's apartment was the only one on this end of the building.

"You nervous?" Caitlin asked. She could tell that Emma was just as nervous as Regina was.

"You have no idea."

Caitlin knocked on the door. To Emma, the wait seemed excruciating. She kept telling herself that it wasn't a date, and she was hoping it wasn't to Regina either. She had nothing against Regina, she was just really nervous. Behind the door, she could hear laughing and the running of little footsteps. It must be Henry. Then, she could hear heels clicking on the ground. It was Regina. The intensity rose in Emma's stomach, and her heart began to race.

As Regina opened the door, Emma's jaw dropped. Before her was standing a gorgeous woman in a short black dress and heels. Her hair fell perfectly around her face, and her makeup was flawless.

"Too much?" Regina asked, slightly laughing.

"You look . . . amazing." Emma said, gathering her thoughts.

"I see you've met Caitlin. Did you get Henry's snacks?" Regina asked, raising an eyebrow at Caitlin. The young woman held up a bag and smiled.

"Well, come on in. Emma, I'm almost ready, I just have to put away my things." Regina said, walking down the corridor to her bedroom.

Emma and Caitlin entered the apartment. To her immediate right, she saw a little boy sitting in the floor watching T.V. She noticed the toys scattered out in the floor, too. The boy looked up at her and smiled.

"Hey, buddy," Caitlin said, picking up the boy. "Emma, meet Henry." Emma smiled and waved. "Henry, tell Emma hey."

"Hi Emma!" he said. It warmed Emma's heart to see his face light up as he said that.

"Well, I see you've met my son," Regina said, walking into the living room. Regina smiled as she looked over to Henry. She took him from Caitlin and headed towards the door. She set him down and put her forehead to his. "Be good for Caitlin. I'll be back later tonight," she said. "I love you, my little prince."

Emma watched as Regina interacted with her son. She was so good with him, so gentle. This was what she wanted growing up. She wanted a loving family. She wanted a parent or parents who loved her. Seeing Regina with Henry like that reminded her of the family she wanted.

"Well, are you ready to go?" Regina asked.

* * *

*An Hour Earlier*

Regina was in the shower. She ran her fingers through her hair and breathed in deeply. She didn't know how she was going to get through tonight. Even after Caitlin's little pep-talk, she was still nervous. She didn't even remember meeting this girl, let alone asking her out. What if this turned out to be a disaster?

A few minutes later, she stepped out of the shower to find Henry standing in the doorway. She quickly grabbed her robe and wrapped it around her body.

"Sweetie, what are you doing in here?" she asked her son.

"Why are you taking a shower now mommy? It's not bedtime yet." Henry said.

Regina closed her eyes and sighed. What was she going to tell him? That she was going on a date? She couldn't.

"I'm having dinner tonight with a nice young woman tonight," she said, wrapping a towel around her head. She walked over to her son. She bent down and grabbed her son's chin, "Don't worry, buddy. Tomorrow is gonna be a Mommy & Henry Day." Henry's face lit up as he wrapped his arms around his mother's neck. He always enjoyed the days he could spend alone with his mother. "Okay, now go play so mommy can get ready."

Henry ran back into to living and continued to watch cartoons. Meanwhile, Regina began to get ready. She scoured her closet in search of a dress. Not just any dress, though; she wanted to wear the perfect dress to take Emma out tonight. Even though she couldn't remember She finally settled on the black cocktail dress that was hanging in the back of her closet.

Within the next twenty minutes, Regina was almost through getting ready. She was putting the finishing touches on her makeup when her phone buzzed. It was Emma.

E - Hey, uh, I'm downstairs. I know, I'm early.

Regina felt a knot begin to form in her stomach. She wasn't ready yet, and Caitlin wasn't back from the store. She decided to text her back.

R - Okay. I'm not quite ready yet. Come on up. I'll buzz you in. Number 108.

After she hit send, Regina entered rush mode. She quickly finished her makeup and grabbed the first pair of black heels she could find. She went back into the bathroom to check herself one more time.

"This is as good as it's going to get, I suppose," Regina said to herself.

There was a knock at the door. Regina began to walk into the living room when the thought of Caitlin hit her mind. How was she going to stall Emma until Caitlin got back?

That was her last thought before she opened the door to find Caitlin and a gorgeous, young blonde woman standing before her. The blonde was wearing a short pink dress black heels, and her golden locks fell perfectly over her shoulders. Regina snapped out of her own trance to notice that Emma was standing there with her mouth open, as if in shock.

"Too much?" she asked, letting a little laugh escape her lips.

Emma blinked as she collected her thoughts. "You look . . . amazing."

"I see you've met Caitlin. Did you get Henry's snacks?" Regina asked, raising an eyebrow at Caitlin. Caitlin smiled and winked at the older woman as she held up the bag. "Well, come on in. Emma, I'm almost ready, I just have to put away my things." Regina said, walking down the corridor to her bedroom.

She closed the door behind her and sighed. How could she not remember that? There was a noticeable age difference, but damn, how could she get lucky enough to score a date with a woman like that?

She collected herself and went back into the living room. When she arrived, she saw Caitlin holding Henry. She glanced over at Emma to see her waving and smiling at him. He seemed happy, and that's all Regina needed to see. Henry was always a very reserved kid. To see him look at Emma like that meant that he saw something good in her.

"Well, I see you've met my son," Regina said. She smiled as she looked over to Henry. She took him from Caitlin and carried him towards the door, before setting him down and putting her forehead to his. "Be good for Caitlin. I'll be back later tonight. I love you, my little prince," she said as she kissed his nose. Regina stood up and looked at Emma.

"Well, are you ready to go?" she asked. Instead of nervousness, she felt contentment following the question. She was ready for tonight.


	6. The Date

**Hey guys! Sorry it's been so long. Life, you know? Anyways, this is a revision of the previous Chapter 6. I was reading through it and thought it needed a little bit of rewriting. I hope to have a new chapter up in the next week or two. Where do y'all want to see this story go? I would love to hear feedback from all of you!**

* * *

"So, to be quite honest, I don't really remember much about last night," Regina said, taking a sip of her water. She and Emma were sitting in the middle of Veronica's, the renowned high-end bistro in upper Manhattan. Around them were many couples dining.

"I wouldn't doubt it," Emma laughed. "I'm surprised you were even able to walk home."

Regina chuckled at the statement. "Well, would you care to enlighten me? From beginning to end, please."

"Okay, so I walk into the club, planning to stay sober anyway so I could drive my sister home, and as I go get drinks, I notice this beautiful, sexy, goddess of a woman sitting next to me looking all depressed," Emma says, grinning and raising an eyebrow. "So, I say to myself, 'Emma, what would be the right thing to do?' Finally, after I order my drinks, I work up enough courage to ask if you were okay. That's when you told me about Henry. When I took the drinks to my sister, you told me you were going home." Emma smiled and straightened up in her seat, "So, being the 'good Samaritan' I am, I insist on walking you home."

As Emma continues her story, Regina just sits and listens. Every time she expresses the way she did or said something, Regina smiles. She watched Emma's every movement, and with every hand motion or excitement in her voice, Regina could see why even in her drunken state she asked her out.

"So, yeah, I guess that's it." Emma smiled.

"Well, I'm delighted that I picked up such wonderful, beautiful lady at Smash. So, tell me a little bit about yourself, Emma." Regina said

Emma grabbed the back of her neck and chuckled lightly, "Well, there's not much to tell really. My sister and I were both in and out of the foster system until we were 18. I moved here immediately for school and my sister was just able to move here a few days ago. That's why I feel like I could almost relate to Henry; you said he was adopted, right?"

Regina smiled at the thought of her precious boy. "Yeah, I adopted him when he was just a few weeks old."

"Well, he is lucky to have such an amazing mom like you," Emma smiled, reaching across the table to hold Regina's hand.

As the evening progressed, Regina talked about her childhood, her family, and why she moved to New York. Emma intensely listened, hanging on to every word that escaped Regina's lips. She wondered how a woman as beautiful as Regina could still be single. She was smart, funny, not to mention being drop-dead gorgeous. Finally it came time for the check to arrive; Regina paid although she received some protest from Emma.

After leaving the bistro, the ladies decided to take a walk in Central Park.

"So, Emma, I know you said you came to the city for school. What are you studying?" Regina asked.

"I'm studying to be a private investigator. I want to start a group to where if kids want to find their parents or any other family members they can." Emma said, staring at the ground.

"Not to be intruding or anything, but don't they already have groups like that?" Regina asked, hoping not to sound too personal.

"They do but they're pretty expensive and you have to have a picture or the name of who you're looking for," Emma said.

"That's understandable. What made you want to choose that career path?"

"I, uh, wanted to find my parents. I want to ask why they gave me and Ruby up. I was only about three and a half, maybe four, when they gave us up. I don't even remember what they looked like. I just don't know why they would keep me for a little bit and, as soon as Ruby's born, give us up." Emma said, looking at the ground. She knew it would be a touchy subject considering Regina's son was adopted.

Regina felt an immense sadness consume her. Emma had been through so much. She and her sister were the unlucky ones in the foster system. Henry could've been one too if she hadn't have adopted him. And she couldn't imagine what going through that must've been like.

"That's an understandable reason . . ." Regina said. She had always maintained a fear that Henry would grow up with questions as to who his parents were and why they gave him up. "I don't know how someone could give up their child, especially for having them for a while and growing a bond with them."

"I can understand at birth, maybe. I know sometimes the circumstances aren't always the best. But what I can't see is holding on to a child for years and then when another comes, give them both up. I just wonder if they have some type of resentment for what they did, you know?"

Regina looked at her. She looked into deep green eyes, and she could almost see the pain that Emma had been feeling her entire life. Regina looked down at her feet as she shook her head. Then she looked back up at Emma. They stopped walking. Emma gently grabbed Regina's face and pulled her closer to her. Their lips met in a sweet, tender kiss. Regina opened her mouth, wanting more of the blonde's taste. Emma gladly followed the older woman's movements. As they pulled away, they both smiled.

"Well . . . that was . . ." Regina started.

"Amazing . . ." Emma continued. Emma cupped Regina's face, pulling her in again. This time, the kis was a bit rougher. There was more wanting, needing from both Emma and Regina. As Regina wrapped her arms around the blonde's neck, Emma moved her hands to the brunette's waist, pulling her closer.

Regina pulled away. "Emma . . ."

"I'm sorry . . ." Emma says, looking down.

"Don't be," Regina said. "Why don't we head back to my place for a drink?"

"I'd love that." Emma smiled.

* * *

 **Don't forget to like/follow/review. Also, follow me on Tumblr Swen1999**


	7. Awkward

**I am back! This is a super short chapter, but I now have some support to help me finish this** **fic! Follow me on twitter swen1999 for updates regarding this fic and when I'll be publishing further chapters. Thanks for reading!**

Regina's back hit the wall of the elevator. Her arms rested around Emma's neck. Emma's hands explored Regina's body as they traveled up to Regina's apartment. Tongues fought for dominance. Regina left out a soft moan as the elevator opened. Emma backed out slowly pulling Regina with her, never losing contact. They stopped when they got to the door of the apartment.

"Emma . . ." Regina said, pulling back. "We need to stop for a second to catch our breaths before we get inside."

"You're right," Emma said with a sigh. "I would hate for your babysitter to think bad of me on our first date."

Regina rose her brow and smiled. "And what makes you think you'll get a second date?"

"Let's just say, I'm a very confident woman." Emma said smirking.

"We'll just have to see about that . . ." Regina said, leaning in to kiss Emma again.

The almost kiss was interrupted by Caitlin opening the door. A smirk ran across the girl's face. She looked at Regina, then at Emma, and then back at Regina.

"You know I can take Henry to my place if you want." Caitlin said, with a soft chuckle.

Regina straightened herself. "That won't be necessary at the moment, Caitlin." She looked at Emma.

"So about that drink?" Emma pondered.

"Of course. The bar is inside. Help yourself. I'm going to stay out here for a moment to talk to Regina." Caitlin said.

Emma entered the apartment while Regina stayed behind to talk to Caitlin. She was all smiles and blushes as Caitlin looks her up and down.

Caitlin smirks. "So, young lady, what took you so long tonight? And inviting her for drinks? On the first date? You must really have an interest in her."

"She's just so… I don't even know how to explain it. I've never hit it off with anyone on a first date like this before. I didn't even feel this way with Mal." Regina said, blushing. "I don't know what I'm feeling right now, but whatever it is I like it."

"Look, I'm not trying to tell you what to do here, but also remember, you've only known this girl for one day."

"I know, but… I don't know. Just in one night she's made me feel… different. Plus she's gorgeous. I mean, damn, have you looked at her?"

"I just want you to make sure this is what you want." She looked into Regina's eyes. She could tell that this is what the older woman truly wanted. Happiness. She hadn't seen Regina truly happy since the day she adopted Henry. Since then, it's like Regina's been in a rut, just going through the motions.

"It is. So can we please go in there so you can get to know her? Your opinion matters to me. I want you to get to know her before she gets too close to Henry. Tell me what you think."

"I'd be happy to." Caitlin said


End file.
